Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization

Motohiro Hirai, Shumpei Terada, Hiroaki Yoshida, Kenki Ebine, Tomoaki Hirata, Osamu Kitagawa

Research output: Contribution to journalArticle

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Abstract

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity strongly depended on the substituent (R2) at the C4′position, amount of NaBH4, and reaction temperature.

LanguageEnglish
Pages5700-5703
Number of pages4
JournalOrganic Letters
Volume18
Issue number21
DOIs
StatePublished - 2016 Nov 4

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Quinazolinones
Enantioselectivity
Derivatives
catalysts
Catalysts
Kinetics
kinetics
synthesis
products
Temperature
temperature
4-hydroxyquinazoline

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization. / Hirai, Motohiro; Terada, Shumpei; Yoshida, Hiroaki; Ebine, Kenki; Hirata, Tomoaki; Kitagawa, Osamu.

In: Organic Letters, Vol. 18, No. 21, 04.11.2016, p. 5700-5703.

Research output: Contribution to journalArticle

Hirai, Motohiro ; Terada, Shumpei ; Yoshida, Hiroaki ; Ebine, Kenki ; Hirata, Tomoaki ; Kitagawa, Osamu. / Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization. In: Organic Letters. 2016 ; Vol. 18, No. 21. pp. 5700-5703
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